

On The Brink with Castle Island
Castle Island Ventures
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
Mentioned books

Mar 6, 2023 • 39min
Michael Gronager (Chainalysis) on Building a Blockchain Analytics Juggernaut (EP.403)
Chainalysis CEO and co-founder Michael Gronager joins us for an episode chronicling the rise of the blockchain analytics firm. In this episode: Michael’s origin story and how he went from helping build Kraken to founding Chainalysis Responding to early market pull from the public sector when building products Responding to criticism around privacy vs. anonymity Building the Crypto Adoption Index for content marketing around what is actually happening on the blockchain Perspective on how long it can take to change an industry online Content mentioned: Public Key (Podcast) Global Crypto Adoption Index Chainalysis Content / Blog

Mar 3, 2023 • 32min
Weekly Roundup 03/03/23 (Silvergate in trouble, Oasis hacks back, Regulation by Blog Post) (EP.402)
Matt and Nic are back for news and deals of the week. In this episode: Is Yuga Labs’ NFT collection on Bitcoin genuine? Will the environmentalist attacks on PoW move to other industries? FTX’ Nishad Singh pleads guilty Ramnik Aurora maxed out donations to George Santos Silvergate is in trouble Why concentration risk makes it difficult for smaller banks to bank crypto firms UK banks are curtailing their crypto exposures Oasis returns $140m stolen from Wormhole to Jump NY Mag’s piece on Arthur Hayes Gensler continues to make vague threats against the crypto space Gensler’s regulation by blog post Greyscale’s case against the SEC is moving to oral arguments Can Bitcoin just change the code and move to PoS?

Feb 27, 2023 • 1h 5min
Matt Cutler (Blocknative) on block building and the economics of MEV (EP.401)
We host Matt Cutler, CEO and co-founder of Blocknative, in this episode to discuss the intricacies of block building and his thoughts on the future of MEV. We cover: The phenomenon of certain block builders subsidizing transactions The requirements for operating a competitive block builder Margins required for sustainable block building MEV redistribution and balancing interests of users vs. validators. You can follow Matt @mcutler on Twitter and learn more about Blocknative here.

Feb 24, 2023 • 39min
Weekly Roundup 02/24/23 (SEC vs Terra, Stables as Securities, the CoinBASE L2) (Ep.400)
Matt and Nic are back for the 400th episode of OTB! In this roundup: Nic’s Vespa story More on Ordinals Is embedding non-economic data in Bitcoin Satoshi’s vision? How Ordinals accelerates efficiency improvements in Bitcoin More FTX crime family news SBF is hit with four new criminal charges Augustin Cartens claims that crypto has lost the battle against fiat NYAG vs Coinex The SEC alleges that UST is a security - does this implicate other stables? What can Congress do about Choke Point 2.0 or SEC overreach Rep. Emmer introduces an anti-CBDC bill Matt’s baseball card collection Silvergate is the most shorted stock right now The SEC blocks Binance.US’ purchase of Voyager assets

Feb 22, 2023 • 53min
Casey Rodarmor on Ordinals, Inscriptions, and Digital Property Rights (EP.399)
Bitcoin developer Casey Rodarmor joins us to talk ordinals, inscriptions, and digital collectibles on Bitcoin. In this episode: What is an ordinal? Why the name? The history of ordinals and inscriptions How does ordinal theory work exactly? How to participate in ordinals and do you need Ord The interaction between inscriptions and Bitcoin fees Should inscriptions be compressed? How should this happen? Why did Casey not use Counterparty? How Bitcoin is the most premium blockspace for NFTs Inscribed content property rights on Bitcoin versus Ethereum Will Bitcoin state just be pruned? Who will store inscription data? How bitcoin data availability might be improving over time How ordinals affect Bitcoin’s security budget Why NFT traders are looking at Bitcoin for the first time Where the inscription 400kb limit comes from ‘Ripping a 4 megger’ Is Casey concerned about out of band transactions Do ordinals actually increase the possible efficiency of operating a full node? The primary bottlenecks in running Bitcoin Core and how inscriptions affect that Will ordinals catalyze more pruning in Bitcoin Core? Might ordinals make rollups more likely on Bitcoin? Do inscriptions dilute Bitcoin’s primary purpose as a monetary system? Transporting other NFTs to Bitcoin with teleburns What Casey is most excited about with ordinals Further reading: Ordinals.com Rodarmor.com Casey's twitter

Feb 20, 2023 • 45min
Ray Hindi & Jake Lynch (L1 Digital) on Crypto Funds, RWAs and DAOs (EP.398)
Ray Hindi and Jake Lynch of L1 Digital join the show. In this episode we discuss: L1 Digital’s origin story and early path into the crypto ecosystem. The firm’s approach to investing in managers and making direct investment. The evolution of crypto funds including views on structure, strategy, focus. The fundraising landscape – how pensions/larger pools of capital think about crypto investing. Views on the impact of FTX. Thoughts on the current regulatory landscape. Real World Assets (RWAs) and how L1D is exploring this thematic area. DAOs and how this framework is evolving. To learn more about L1 Digital visit L1.Digital.

Feb 17, 2023 • 40min
Weekly Roundup 02/17/23 (BUSD Wells notice, Howey vs Reves, the SEC’s custody guidance) (EP.397)
Matt and Nic return for another week of news and deals. In this episode: Is peak FUD in? Is this the ‘custody rule rally’? OTB is keeping the deals of the week House is probing the connections between FTX and the SEC SBF is banned from using a VPN Is SBF a secret sports fan? SBF’s bail cosigners are unmasked SBF VC investors are hit with a class action lawsuit SEC sends Paxos a Wells notice Circle dispells Wells notice rumors Is the SEC going after all stablecoins or just BUSD? What does Reves say about stablecoins being securities? Tether is the beneficiary of the crackdowns in the US Can US regulators really go after Tether? How Paypal deposits are like stablecoins What’s in the SEC’s custody rules? Changes to market structure if the SEC’s custody rules go through Binance suggests that they are ready to settle up with US regulators

Feb 10, 2023 • 49min
Weekly Roundup 03/10/23 (Choke Point 2.0, staking in the crosshairs, ordinals take off) (EP.396)
Matt and Nic return for another week of news and deals. In this episode: Kraken winds down their staking as a service product The SEC asks all staking as a service providers to register Does 3rd party staking pass all of the prongs of Howey? The FT’s article on the final days of FTX Did the FTX executives leave the labradoodles in the Bahamas? Ordinals are bringing NFT enthusiasts to Bitcoin Matt has had a tough week Kyle and Su launch OPNX So what’s the deal with the crypto-focused Chokepoint 2.0? Major crypto-facing banks are cutting back their crypto practice What will be the fate of the Wyoming SPDIs? The boys review Bad Boys We discuss Colombia’s hippo problem DCG reaches a provisional agreement with creditors Our Storybook Brawl conspiracy Content mentioned: Nic in Pirate Wires, Operation Choke Point 2.0 Is Underway, And Crypto Is In Its Crosshairs Sponsor notes: Subscribe to the Coin Metrics State of the Network newsletter

Feb 6, 2023 • 59min
Josh Benaron (Bundlr) on the Importance of Permanent Storage and Provenance (EP.395)
In this episode, we were joined by Josh Benaron, founder of Bundlr, a scaling protocol built on top of Arweave. Josh shares his views on: Censorship resistant and permanent storage The importance of provenance in attributing and distributing value Why Arweave's approach to decentralized storage is elegant How Bundlr addresses trade offs in Arweave and makes it more usable Follow Josh Benaron here. Learn more about Bundlr here.

Feb 3, 2023 • 54min
Weekly Roundup 02/03/23 (Ordinals frenzy, Charlie Munger, Tether truthers are back) (EP.394)
Matt and Nic return for another week of news and deals. In this episode: Nic’s Proof of Reserves for Policymakers Charlie Munger attacks crypto The academic Tether truthers are back We unveil a new bad boy New allegations about Celsius surface The problem with exchange tokens How do you retire a token? The paradox of issuing tokens via an offshore foundation SBF is allegedly tampering with witnesses Did Sam really believe in EA? We review Mel Gibson’s Apocalypto Were the Maya really that bad? What on earth is going on with Ordinals? Are Bitcoin NFTs a DOS attack? A conflict of visions in Bitcoin reemerges Matt keeps tearing his shirts VC dress codes Content mentioned in this episode: Ark Invest Big Ideas 2023 Report Coin Metrics’ report on MEV Dennis Porteaux, Illegitimate Bitcoin Transactions Nic Carter, Proof of Reserves for Policymakers