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    Business

    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

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    Latest Episodes:
    OTB Live! Weekly Roundup 09/23/22 (EU's MiCA regulation finalized, XRP lawsuit, SEC dings Balina, Audience Q&A) (EP.352) Sep 23, 2022
    Show notes

    Nic and Matt sit down for a special live recording of OTB in front of an audience at the Boston Blockchain Week. In this episode:

    • Ian Balina is dinged by the SEC for Sparkster
    • The SEC's weird argument for standing over all of Ethereum
    • Is XRP a prediction market on Ripple's case against the SEC
    • Wintermute is hacked for $160m via a bad vanity generator
    • Several Senators file an amicus brief to support Custodia's lawsuit against the Fed
    • What the Congressional crypto agenda should look like
    • Europe finalizes their MiCA regulation
    • Europe discourages Dollar stablecoin usage in the EU
    • Exchanges and token issuers in the EU will have to make disclosures
    • Jesse Powell steps down from Kraken
    • NASDAQ is launching a crypto custody business
    • Helium strikes a deal with T Mobile
    • Audience Q&A

    Sponsor notes:

    • Talos powers institutional access to the entire digital assets ecosystem via a single-point of entry. Connect directly to your preferred prime brokers, lenders, investors, custodians, exchanges, OTC desks and more, or meet them on Talos. Get started at Talos.com

    • Subscribe to the Coin Metrics State of the Network newsletter

    Steven Goldfeder (Offchain Labs) on Building Arbitrum (EP.351) Sep 19, 2022
    Show notes Steven Goldfeder is Co-Founder and Chief Executive Officer at Offchain Labs, the team building Arbitrum. In this episode we discuss:
    • Steven's academic background, and his work at Princeton University.
    • BlockSci, an early blockchain forensics/search product that Steven co-founded.
    • The evolution of MPC custody and the exciting developments in that category.
    • The Flash Boys 2.0 paper and the current state of MEV.
    • Steven's views on the evolution of L1 smart contract platforms and how L2 scaling is shaping up.
    • The design choices and considerations that went into the choice of optimistic vs. zero-knowledge rollups on Arbitrum.
    • The future of ZK systems on blockchains.
    To learn more about Arbitrum and follow Steven visit www.offchainlabs.com

    Weekly Roundup 09/16/22 (Merge makes it, Chainalysis crypto adoption report, Starbucks NFTs, Coinbase grades Congress) (EP.350) Sep 16, 2022
    Show notes

    Matt and Nic return for another week of news and deals. In this episode:

    • The Merge takes place without incident
    • Will the Merge silence Ethereum critics on the left?
    • Will the ESG narrative around crypto get louder?
    • FTX takes a stake in Skybridge
    • Castle Island is not an island
    • If you make an NFT of a diamond and destroy the diamond, do you still have a diamond?
    • CME launches Ether options
    • Starbucks launches an NFT loyalty platform
    • Tungsten cubes are selling off
    • South Korea issues an arrest warrant for Do Kwon
    • The thin line between visionary and scammer
    • What Terra teaches us about why disclosures matter in capital markets
    • Huobi delists privacy coins
    • Can you take delivery of Tornado Cash-dusted Ether?
    • Coinbase launches their Crypto Action Network
    • Matt and Nic evaluate the ratings members of Congress are getting from Coinbase
    • Chainalysis releases their 2022 global crypto adoption index
    • Hodlnaut's CSW case begins
    • The NSA Bitcoin lab leak hypothesis
    • OTB goes live!

    Mentioned in this episode:

    • Jake Chervinsky's thread on Tornado Cash
    • Chainalysis 2022 Global Crypto Adoption Report

    Sponsor notes:

    • Talos powers institutional access to the entire digital assets ecosystem via a single-point of entry. Connect directly to your preferred prime brokers, lenders, investors, custodians, exchanges, OTC desks and more, or meet them on Talos. Get started at Talos.com

    • Subscribe to the Coin Metrics State of the Network newsletter and read their Mapping out the Merge report

    Dan Mottice (Ansible Labs) on Building the Offramp for Web3 (EP.348) Sep 14, 2022
    Show notes

    Dan Mottice, CEO and Co-Founder of Ansible Labs, joins the show to talk about a new payment gateway for web3.

    • Dan's personal background and how he ended up in financial services
    • The Visa Network, Visa Direct Payouts and Visa Crypto
    • Ansible Labs' raise and what's ahead
    • Off-ramps and why they matter
    • North stars in fintech
    • The consumer experience in a b2b sales cycle
    • Navigating turbulent markets and how to build to win

    Learn more about Ansible here.


    David Hoffman (Bankless) on Everything About the Merge (EP.349) Sep 14, 2022
    Show notes

    Bankless' David Hoffman joins Matt and Nic for a special episode to cover Ethereum's highly-anticipated Merge. In this episode:

    • How David came to Ethereum and the Bankless origin story
    • The story behind the Bankless DAO
    • Whether David would ever consider focusing on other blockchains
    • What could cause David to abandon Ethereum
    • The Coinbase OFAC filtering debate
    • Why proposer-builder separation might make validator-driven censorship harder
    • Filtering transactions at the pool layer versus undertaking a 'Treasury Activated Soft Fork'
    • Under what conditions would social slashing of major validators make sense?
    • How embedded is the social slashing consensus into Ethereum's social fabric?
    • The significance of the new supply dynamics stemming from the Merge
    • Is the unlock something to worry about?
    • Is there a 'crowding out' effect from staked Ether becoming a risk free rate?
    • Does MEV pose a concentration risk post Merge?
    • Are MEV-driven yields for stakers perverse?
    • Is MEV an inescapable feature of richly stateful blockchains
    • Why the notion of Certified-Toxic-MEV-free blocks might emerge
    • How is Ethereum's roadmap determined?
    • What's the deal with the Surge, the Verge, the Purge, and the Splurge?
    • What are the strongest narratives coming out of the Merge?
    • Probabilities of the Merge success
    • Why the Merge may not be fully priced in

    Follow David on Twitter and learn more about Bankless.

    Intro and outro music: Daniel Allan's Collage #344


    Weekly Roundup 09/09/22 (Stablecoin wars, White House energy report, Gensler attacks) (EP.347) Sep 09, 2022
    Show notes

    Matt and Nic return for news and deals of the week. In this episode:

    • Nic's shoe problem
    • Web3 merch for OTB?
    • The White House releases a report on crypto asset energy usage
    • Why the US should encourage mining within its borders
    • Coinbase is funding a lawsuit against OFAC
    • Binance is converting USDC into BUSD on their platform
    • Poolin is having liquidity problems
    • Russia considers crypto for cross border payments
    • The US Government recovers $30m from the Axie hack
    • Gensler keeps firing barbs
    • Nic doesn't buy the supply shock thesis around the Merge
    • Will ETH have another high fee era?
    • What could an ETH carry trade look like?

    Content mentioned:

    • The White House, Climate and Energy Implications of Crypto-Assets in the United States
    • Gary Gensler speech at the SEC, Kennedy and Crypto

    Sponsor notes:

    • Subscribe to the Coin Metrics State of the Network newsletter and read their Mapping out the Merge report

    Bennett Collen and Stephanie Howard (Endstate) on building a web3-native fashion brand (EP.346) Sep 06, 2022
    Show notes

    Ria and Nic from Castle Island sit down with Stephanie Howard and Bennett Collen, cofounders of Endstate, a web3 footwear and fashion brand. We cover the merits of the redeem-and-retain NFT model and the vision for Endstate.

    • Bennett's prior crypto startup and how he decided to unite his passion for sneakers with web3
    • How Bennett and Stephanie met and cofounded Endstate
    • Stephanie's career in sneaker design to date
    • Why creators and athletes are jumping at the opportunity to issue merchandise-linked NFTs
    • Why Bennett and Stephanie chose to launch a web3 native brand
    • How redeem-and-retain NFTs allow manufacturers to reduce inventory risk
    • Why fashion is getting more targeted and niche
    • Why Endstate is able to release new iterations of their sneakers so quickly
    • Endstate's rationale for manufacturing in the US
    • Endstate drops to date
    • Endstate's new drop with Eagles wide receiver DeVonta Smith
    • How web3 brands should think about which metaverse to build for
    • Endstate's thinking around Solana vs Ethereum and the impact of gas fees
    • How to link physical products with NFTs – from NFCs to QRs to visual scans
    • What should we call physical NFTs?
    • Aside from shoes, what merch is amenable to the Endstate model?
    • What product sectors will be NFTed?
    • How developed are authenticated third party marketplaces for physically linked NFTs?
    • Physical-linked NFTs as a trojan horse to onboard mass markets into web3
    • The future state of Endstate
    • Other web3 drops Bennett and Stephanie enjoyed
    • The future of entangled NFTs

    Read more:

    • Nic Carter on Medium: Redeem and Retain NFTs are the future of Luxury Goods
    • Vogue Business: How the crypto bear market is resetting fashion's Web3 strategy

    Drops and more at endstate.io

    Intro and outro music: Daniel Allan's Collage #344


    Weekly Roundup 09/02/22 feat. Kyle Waters (Merge priced in, Roche and Ava Labs, Will Dai float freely?) (EP.345) Sep 02, 2022
    Show notes

    Matt and Nic return for another week of news and deals. In this episode:

    • What happens to the GPUs post merge?
    • Will the gamers finally get cheap GPUs back?
    • Is the merge like superbowl sunday or Y2K?
    • Does the success of the merge undo a long-term Bitcoin talking point?
    • Are NFTs going to cc0 screwing over their users?
    • DC sues Michael Saylor and Microstrategy for allegedly skipping taxes in DC
    • The SEC questions whether the certain assets in Grayscale trusts are securities
    • What's going on with the Roche Freedman/ Ava Labs/ Cryptoleaks situation?
    • Is Roche just David Boies 2.0?
    • The Biden executive order reports are due next week
    • Rune of Maker muses about turning Dai into a free floating unit of account
    • Will Maker be able to survive real world assets as collateral?
    • Did Moonbirds rugpull their buyers with IP issues?
    • Kyle Waters from Coin Metrics joins to talk about the Merge
    • Is the distribution of stakers on Ethereum something to be worried about?
    • What's going to happen to ETH issuance post merge?
    • How to forecast post-merge staking returns
    • Is the merge priced in?
    • Did Ethereum install a pro-cyclical monetary policy?

    Content mentioned:

    • Coin Metrics, Mapping out the Merge

    Sponsor notes:

    • Subscribe to the Coin Metrics State of the Network newsletter

    Obi Nwosu (Fedi) on Second-Party Custody with Fedimint (EP.344) Aug 29, 2022
    Show notes

    Obi Nwosu, CEO and Founder of Fedi joins the show to cover a new model for shared Bitcoin custody in Fedimint. In this episode:

    • Obi's experience with Coinfloor and how that informed his views on custody
    • Why third party custody with Proof of Reserves isn't sufficient
    • Why 'credible centralized' custody shouldn't be the default
    • Why state level attacks on custodians are ramping up
    • Obi's early prediction that Nigeria would be the heartland of Bitcoin adoption
    • Why messaging apps are actually the most popular p2p exchanges worldwide
    • The history and origins of Chaumian Mints
    • How the enabling pieces of Fedimint all came together over time
    • The relationship between federated custody and microfinance
    • How Fedimint is analogous to Free Banking
    • Does Fedimint satisfy Hal Finney's vision for Bitcoin banks?
    • How Fedimint compares to first party custody
    • How Obi expects regulators to react to Fedimint

    Learn more about Fedi and Fedimint.


    Weekly Roundup 08/26/22 (Emmer's OFAC letter, Stables resist TC blacklists, Gensler's OpEd) (EP.343) Aug 26, 2022
    Show notes

    Matt and Nic return for news and deals of the week. In this episode:

    • Matt's prior radio career
    • The boys consider reinvesting in the podcast
    • How to avoid audience capture
    • We puzzle over metaverse advertising
    • How do you value metaverse real estate?
    • Rep. Tom Emmer writes a letter to OFAC questioning their sanctioning of Tornado Cash
    • Tether and BUSD (Paxos) don't blacklist Tornado Cash addresses
    • The FDIC reprimands crypto companies
    • Web3 hoodies
    • Best podcast listening speeds
    • Are security tokens and real world assets back?
    • No new 3ac shenanigans
    • Tadge Dryja leaves MIT DCI for David Marcus' Lightspark
    • New findings on OFAC censoring Bitcoin Mining pools
    • Tether has a new auditor
    • Can a firm with outstanding tokens be acquired or go public?
    • Gensler's weird op-ed

    Sponsor notes:

    • Subscribe to the Coin Metrics State of the Network newsletter

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