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 01/30/26 (Fidelity’s FIDD, Gold rally, Worldcoin and AI bots, digital alibis) (EP. 698)
On The Brink with Castle Island
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 has 140 tons of gold now Why is Bitcoin not participating in the “debasement” trade? Is gold at risk from alchemy? People are still worried about quantum Will Worldcoin save us from AI bots?...
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Weekly Roundup 01/23/26 (CLARITY stalls, Iran's USDT reserves, Is Web3 Social over?) (EP.697)
On The Brink with Castle Island
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 Kalshi Jeffries drops Bitcoin from its model portfolio over quantum risk Coinbase launches an advisory board on quantum Trump sues JPM for debanking him Does the Central Bank of Iran really...
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Weekly Roundup 01/16/26 (CLARITY problems, InfoFi Dead, CA Wealth Tax, Kontigo) (EP.696)
On The Brink with Castle Island
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 as interesting as stablecoins Content mentioned in this episode: Jason Mikula,
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Wyatt & Jake Lynch on Onchain Financial Markets (EP.695)
On The Brink with Castle Island
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 leave us? What metrics matter for onchain markets? What market dynamics contributed to the October 10 washout? How does leverage manifest in onchain markets, and what does it look like today? How do...
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Weekly Roundup 01/02/26 (2026 predictions, wealth taxes, secret insolvencies) (EP.694)
On The Brink with Castle Island
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 to try socialfi again? Kickstarter snafus Content mentioned in this episode: Nic Carter,
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2025 Highlights and 2026 Predictions with Blockchain Coinvestors (EP.693)
On The Brink with Castle Island
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
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Weekly Roundup 12/19/25 (Quantum FUD, CLARITY markup, are forks obsolete?) (EP.692)
On The Brink with Castle Island
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 Bitwise 2026 predictions The four year cycle is over Grabby aliens and the Dark Forest Content mentioned in this episode: Talos and Factset,
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Corn (Yearn Finance) on the Evolution of DeFi Protocols (EP. 691)
On The Brink with Castle Island
Henry sits down with , head of business development at , 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 state of onchain cybersecurity and recent hacks What is the appetite for defi from non-crypto users and institutions, and will a declining fed funds rate help? How do defi protocols drive value to their native...
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Weekly Roundup 12/12/25 (Do Kwon sentenced, DTC no action letter, Circle’s private stablecoin) (EP.690)
On The Brink with Castle Island
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 stablecoin The DTC gets a no action letter from the SEC to settle tokenized securities We do a Terra/Luna restrospective Terra’s fatal mistake Oracle mishaps on prediction markets Why did the...
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Weekly Roundup 12/05/25 (The trouble with Taproot, a prediction market paradox, HFSC OCP.2 report) (EP.689)
On The Brink with Castle Island
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 Vanguard adds Bitcoin ETFs House Financial Services Committee releases their final report on OCP2.0 What’s going on with leverage in crypto? Are AI agents going to start stealing crypto? Is...
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