Bennett Collen and Stephanie Howard (Endstate) on building a web3-native fashion brand (EP.346)
On The Brink with Castle Island
Release Date: 09/06/2022
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
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Weekly Roundup 10/17/25 (Flash crash, pig butchering scam busted, Erebor charter granted) (EP.678)
On The Brink with Castle Island
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
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Pbj (Perpl) on the Perp DEX Market & Monad's Imminent Launch (EP.677)
On The Brink with Castle Island
Wyatt sits down with Pbj, the founder of , 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 excited
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Dave Balter (Flipside) on the convergence of AI and Blockchain Analytics (EP.676)
On The Brink with Castle Island
Dave Balter, the co-founder and CEO of 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 years. Where Flipside is focusing its efforts within the blockchain data/analytics segment. To learn more about Flipside visit and follow the company on .
info_outlineRia 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